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Annie Griffiths's avatar

I'm 72 and have always loved fashion, despite my tomboy career. I've dressed for work in jeans most of my career, but also need dressier things for speaking appearances. The only guide I trust is clothing that makes me feel good, and I don't care who the designer is. No heels. No beige/brown/grey. Cute sneakers, sundresses, fun pants, international jackets, lots of pashminas. For my son's wedding I wore a crisp white blouse with a full-length skirt covered in enormous blue polka dots!

Step away from Eileen Fisher As my girlfriend said to me recently, "We may be too old for beautiful, but we can always be cute!"

Carol Robbins's avatar

I'm a 65 year old female. I teach movement so I dress in leggings and tees every day. I have a large collection of leggings and since the pandemic I've moved away from black towards brighter colours to show up better on screen. Making that change was difficult but I'm embracing it.

I can only wear clothes that permit a lot of movement - I can't stand restriction, and that includes shoes. All my shoes are "minimal" with wide toe boxes, which look a bit clownish if you aren't used to them. But once you try them you won't go back to toe-pinching shoes again.

The only change I've made is longer, flow-ier tops (surprisingly hard to find for my 6'1" pear shaped frame).

I am curiously drawn to clothing meant for 20 year olds, like the art tees at Uniqlo, which are not age appropriate but I don't care. When I dress up I usually go for baggy dresses, skirts and pants - Japanese style in black.

In terms of dressing your age - I think of what my mom wore at 40, 50 and 60 etc., but I've never dressed like that. Clothing and attitude towards aging has changed a lot since those days. But comfort and ease of movement will always come first; if I can't squat in it without plumber's crack, I don't buy it.

Sari Botton's avatar

You definitely don’t want plumber-butt… Yes to comfort, and yes, the “rules” around older women’s style have definitely shifted, thank goodness.

Tiffany Lee Brown—BurningTarot's avatar

I'd love to hear where you get your wide toe clown shoes. I used to find Keens excellent but since they changed over, the shoes are flimsier and the toe boxes far less roomy on most styles. Recently I discovered Dwarves Shoes "big toe" styles; one boot has been pretty good but I find Dwarves (so far) are not very walkable. Like, they look good and imitate Doc Martens, but they just don't make it easy to walk, which a Doc would do.

I'm usually looking for zero-drop or close to that, preferably with enough head room to fit an orthotic insert. If you have any ideas, I would SOOO appreciate links! Thank you.

Carol Robbins's avatar

Sure! first of all, I'm in Canada/Ontario so depending on where you are you might have more/less options. There's a brand called Shapen that make a Doc Martin alternative, patent leather with laces in the front, zipper on the inside, with zero drop, flexible sole. They are very cool! Avail at Cool East Market in Toronto (or online).

Some easy to find brands are Altra (good cushioning, but still zero drop and wide toe box - perfect for transitioning from conventional shoes), Xero, Lems (I wear their runners and boots). Foot shape and volume can also be a factor so it's a bit of a crapshoot sometime. This is why it's nice to find a place to try them on. My most minimal shoes are Wildlings which I buy direct from EU but they charge duty and end up being expensive. They offer free ship/return on your first purchase so you can get that size right.

Tiffany Lee Brown—BurningTarot's avatar

Thank you! I've looked at Lems before, and will do so again on your recommendation. Never heard of Shapen! Yay, something new to investigate.

I have a pair of now-old and kinda-stinky Altras I originally bought during a serious foot injury recovery -- bright and kind of hideous magenta with screaming Day-Glo orange accents. And that ends up being the only real walking shoe I can wear now. A recent attempted purchase of several Altras including some labeled as the same model -- ended up having way less everything, less toe room, less height, less length. So I'm hoping to try Altra again, and if they work again later for me, maybe they will make non-athletic shoes too.

Xero makes such beautiful shoes. Unfortunately no height to speak of, and my podiatrist is opposed to that barefoot sole for my particular issues.

Carol Robbins's avatar

I specialize in foot health and have transitioned a lot of clients away from commonly prescribed orthotics, but I will often use a thick alpaca insole in my Wildlings particularly if I need to walk on sidewalk/pavement. You could experiment with insoles (sheepskin/alpaca). Altras have a lot of different models yes but I think all are sporty. (Hilariously, my first pr of zero drop were magenta Altras because that's the only colour they had in my size.)

Tiffany Lee Brown—BurningTarot's avatar

We have the same Altras!!

The orthotics are new for me, and they've really helped with a 13-year-past foot injury. Metatarsal pad plus a bit of extra inner arch support.

Unfortunately I am wool-averse though I live in an area where people raise alpacas.

Do Wildlings have -- whatever the word is, like the shoe is tall enough for an insert, and doesn't press on the top of the foot? My main foot injury occurred on the top of my foot and is still easily aggravated, so I can't wear anything that presses on that area. Kind of desperate here, thank you so much for answering all these questions!!

Carol Robbins's avatar

You have what's called a "high volume" foot. So when you are shopping make sure you tell them you have this. Some models (unfortunately the Shapen Docs among them) are better for low volume feet. However, sometimes I find that people who have this high volume also have stiff feet and with a bit of training they can access pronation better and their foot isn't so high and stiff. Good luck!

Nancy Friedman's avatar

You're not going to get demographic data from me; I don't acknowledge birthdays and I loathe generational labels. This is as confessional as I'll get: I've always loved clothes -- my first paying job was as a member of a Los Angeles department store's high school fashion council -- and I've long been a student of fashion. I have a shelf of books about style and the history of clothing, and the one that's made the biggest impact is "The Lost Art of Dress," by the historian Linda Przybyszewski ("Professor Pski" http://www.professorpski.com/). She celebrates the "Dress Doctors" -- home-economics experts -- of the early to mid 20th century, who taught women about proportion, fit, and, yes, standards of beauty and age appropriateness. The 1960s "Youthquake" put an end to that halcyon era: Now we were supposed to celebrate adolescence above all, and feel miserable about our bodies if we weren't shaped like teenagers. There is, after all, something to be said for the privileges of age: worldliness, confidence, elegance. (A caption below a 1952 illustration of gorgeous knee-covering dresses: "It took an older woman, one who moved at a leisurely pace, to wear dinner dresses with a draped bodice or skirt.") There's also something to be said for training your eye on clothing you consider beyond your budgetary reach. For me, that has meant Issey Miyake: expensive, timeless, kinetic, and probably of little interest to a teenager. Last year I finally snagged the Issey Miyake Pleats Please pants of my dreams at deep discount; it was worth the wait. Yes, I wear jeans too (dark wash, subtle barrel shape). But I reject the notion that the only beauty worth honoring is the specific beauty of a 15-year-old girl.

Alicia Dara's avatar

GenX woman here. I recently figured out that my personal style is formulated on a silhouette more than anything else. I like a skinny leg, a skinny arm, crisp shoulders and a waist that’s cinched but not tight. I used to love a med-to-high heeled ankle boot with everything, but my feet don’t want that anymore, so I’ve had to resort to a flatter boot. Overall I like clothes that are slim fitting but have plenty of stretch in the fabric. I refuse to dry clean anything (I’m constantly reminding people that it doesn’t really get clothes clean and is terrible for the environment!!) so I look for a high content of organic cotton, which holds up well in the washer. Mostly my clothes are non-pattered and simple, but I fucking love accessories and outerwear, so I’ll spend more on those things. When I was younger I used to think that everything would look better if I was super-skinny, but now I know that regular strength training (and the bulking up that comes with it) give me wicked-good posture, and that shit is magical. Still miss my high-heeled black boots though!!!

Sari Botton's avatar

I love how well you know yourself and your style, Alicia! And that you like your new shape.

Beth Boyle Machlan's avatar

I miss boots so much! I used to have so many black boots that more than once I mismatched them, back when I had to get dressed for work at 4:45 am! But my plantar fascitis says NOPE.

Adrienne Hand's avatar

Oh how I love this post. Thank you for opening the closet for all of us! We gotta set ourselves free! I struggle with my style which is thrift-store 60s and 70s florals meets chicos practical-&-sometimes-surprisingly-fun, and boho flow. Just a mix that says, “Hey I’ve still got it!” and, “Gotta meet with a client and look respectable.” Confusing, right? I’m 64 but I feel 8 and 26 and 35. And my hair which I hope is light brownish but is actually orangish, has shifted me from “winter” to “fall” on the color spectrum. I just bought 4 tees, culottes (!) and a stretchy dress in olive green to match my eyes. Never done that before, but my sister does and she always looks good. Sigh.

Sari Botton's avatar

Sounds like a great style! And you know I relate to being so many ages at once… <3

Susan Dabbar's avatar

I just turned 65, I dress with intention, not apology. Quality, tailoring, breathability, and self-respect are part of the package. Comfort matters, but so does showing up for myself—and that doesn’t mean fast fashion or disappearing into neutral tones. As a media founder and someone who is public facing on social channels I think about this question a lot.

Your query is timely. We just published this article in my magazine PROVOKEDbysusan.com

that speaks directly to this hot topic.

Melissa Gould wrote, “The Quiet Power of Dressing With Intention" where she explores how American women have been fed a false narrative that dressing down is a form of feminist rebellion—when in fact, dressing well can be an act of quiet, confident power.

Some of the lines that really hit:

“Have we been mistaking comfort clothing for some kind of body-positive, feminist ideal? If so, that’s a bill of goods I’m no longer buying.”

And:

“European women don’t dress well despite feminism. They dress well because of it.”

The piece pushes back on the idea that caring about how you present yourself is vain or performative. It reframes style as agency—especially for women over 50 who’ve spent decades getting dressed for everyone else.

You might enjoy it. It stirred up a big response from our readers—many of whom, like you and your audience, are defining their style as a form of self-respect, not self-erasure.

Sari Botton's avatar

Oh, I love all of this. Will check out the magazine.

Bea Harnish's avatar

My mother was a seamstress by necessity and made all my clothing except underwear. Because of her, my awareness of color, texture, cut, and style was just a part of growing up. I never learned to sew, but I know what I like, and after 81 years, (some of it in a career that demanded a look of competency) I have arrived at just a few requirements: 1. My clothing must be comfortable. 2. My clothing must allow me to believe I am still pretty. 3. Consignment shops are the way to go.

That said, I have one major problem: my changing boobs. During Covid, the point of trying to look nice became, well, pointless. Why put on a bra? I wasn't going anywhere. Now several years later, I chafe at putting on that dang bra. Besides both becoming pendulous, one breast is slightly higher than the other. Those ads about bras for older women? I am such a sucker. None of them work. The super elastic ones ride up and pretty soon, one breast is enjoying freedom while the other dutifully remains covered.

Then there's the sports bra. Can you say uni-boob? No thanks.

If I buy adjustable-strapped-ones, the fit is good until I move around and the straps slip off my shoulders.

My third requirement for clothing is going to have to be ignored. I see myself going to a "bra consultant" if there is such a thing, and spending some good moola to get a good fit. And then who knows? Will my 81 year-old boobs continue to change and therefore they'll need something different?

The interviews I read here indicate that getting older means you care less about what others think about you. Not true for me. I want my girls to be up there, pert, and if not youthful, at least well-defined. Is that "age appropriate?" It is for me. Onward on my quest to find a good bra.

Sari Botton's avatar

I share your frustration on the bra front. I stopped wearing underwire during the pandemic, and so many of the wireless ones give that uniboob you speak of.

Nancy Friedman's avatar

Icebreaker merino wool Queens Clasp bra ftw! No wire, and the cups have three-part construction, which gives them shape and structure. Merino is a miracle fabric that's fast drying and comfortable in all climates. I am such a a big Icebreaker fan that they should put me on the payroll, but I offer this endorsement for free. P.S. The QC bra is currently marked down in the Icebreaker site.

Amy Allsopp's avatar

I have small boobs and I love Icebreaker's Siren bra - breathable merino, just enough support, and no uni-boob.

Nancy Friedman's avatar

Haven't tried that one! (I’m not fan of over-the-head styles — I always get tangled up.) Love the Siren bikinis, though!

Beth Boyle Machlan's avatar

Seconding this! I now basically wear sports bras whenever possible!

Ann-onymous's avatar

Prana brand bras have worked for me. For yoga. Comfortable, no uni-boob.

Sue Sutherland-Wood's avatar

I enjoyed this honesty SO much! One of the (many) reasons I come here to read xo

Elena Brunn's avatar

Some boutiques offer a bra consultant, occasionally called a — corsetiere!

Susan Weis-Bohlen's avatar

You had me at “gaberdine”. I haven’t heard that word for at least 40 years. We were also in the clothing business. Gaberdine, oh my. So, you looked beautiful in the long black dress with the slits. A really colorful scarf in like pink and orange and blue would look amazing with that, emphasizing your hair and eyes. I am a big believer in color www.gudrunsjoden.com. And I also love Flax. Wide leg pants, asymmetrical dresses. Beautiful, rich colors.

It makes me happy and it makes people around me happy. Bright, big colors, polka dots, Indian block prints. It’s like wearing art. I give zero fucks about age in deciding what to wear. Same with my hair. Zero fucks. You do you and if you don’t know who you are, meditate on it! Or go shopping with your two fantastic friends. I love them.

Sari Botton's avatar

Capitalism has run amok, but it really is fun to shop with friends. And I’m trying to embrace color more. I lived in a gabardine-lined world when I worked on Seventh Avenue!

Tiffany Lee Brown—BurningTarot's avatar

Gudrun fan here ,too! Unfortunately they don't carry petites, so mostly I buy a few shapeless cotton dresses on clearance, and a lot of scarves. Yes, filmy scarves or "shawls" do scream Middle Aged, but I don't care. I'm having fun with bright color or fall colors. Recovering Goth.

Elena Brunn's avatar

Something fashion-horrendous happened to me when I retired at 75 during Covid, after teaching bed-ensconced college students over Zoom. My loose size 6 turned into a loose 12. And not coincidentally I went from Eileen Fisher wannabe to 1950s preppy boy: LL Bean shirts, tees, jeans. On inspired days, I slipped on faux ivory bangles or twisted on silver cuffs. Now at 79 3/4, I'm hankering for style again. And fitness. Pilates. Allegedly gentle yoga. The elliptical. I want to look as if I haven't given up. I loved your fashion clips, Sari, and wish you happiness with however you feel like dressing.

Sari Botton's avatar

Thank you, Elena! Hope you find your style again!

Ann-onymous's avatar

Just turned 60. BTW I've looked forward to being 60 all my life; I've just always had an intuitive sense that my sixties would be a GREAT decade for me. Really excited to be sixty, finally!

I'm a clergywoman in a liturgical tradition (which means at worship services and hospital visits I wear a clergy collar) in a conservative community so figuring out what to wear is always an interesting challenge. It is ironic that I went into a field where I often have to wear something around my neck, because as a small child I was famous for stripping off turtlenecks. I've also worked as a hospice chaplain and have a lot of connections with the healthcare field, so a lot of my work-related clothing is super practical and must be machine-washable.

Because of my job, I always need to have something to officiate for a funeral in, which means: black ankle boots (graveyards are often muddy), dressy black slacks (ALWAYS with pockets), black tanks (combines with a clergy "Janie" collar I use a lot) black blazer but with a lot of freedom of movement because I am doing a lot of arm movements at a service. Freedom of movement is extremely important for me.

I do have a couple of pretty fabulous sterling silver pectoral crosses for work; once I was questioned on the purchase of one, because I'm clergy-ing while female and the salesperson didn't know women could be pastors.

Stylewise: A surprising amount of my clothing comes from a local outdoor gear store -- think Smartwool, Kuhl brands. I have some of the travel line clothing from Chico's, Talbots. SOME hospital scrubs look like slacks; I use those for hospital and some field / home visits, where I can just throw everything in the wash.

I do wear Eileen Fisher pieces (not a lot, but the ones that work for me) and have done since my thirties. I like Flax brand as well; again, one has to be careful, some stuff is too boxy for me but some items have worked really well for me. I live in a very hot, humid location in the summer so I have several linen and cotton dresses. I have some sleeveless A-line African print dresses with pockets (brand name is Zuri). Aside from the print dresses, I tend to prefer to keep my clothing fairly basic and neutral so I can go ALL OUT on bags and scarves! My favorite scarves come from a designer in Brooklyn, Juli Raja.

In my thirties, I got plantar fasciitis for the first time, and a physical therapist friend looked deep into my eyes and said, "Your fun, cheap, cute shoe days are over." Sadly, she was right.

Sari Botton's avatar

Interesting! Your vocation adds challenges. (Brought to mind the words “funeral officiant-chic.) I, too, got plantar fasciitis in my 30s. I got it from running. Was hard to heal, and that has informed my footwear choices since.

Erika Andersen's avatar

Loved getting this personal glimpse into you, Sari - and I love how you’re evolving your style, based on what feels like you.

I realized, as I read your article, that for some wonderful reason, I never think about “dressing my age,” even though I’m 73. I really only think about what’s comfortable, and what I think is pretty and flattering. Since I mostly retired from interacting with clients two years ago, my wardrobe is much simpler, and I’ve given away most of my “business clothes.”

I mostly wear black Yoga pants, lighter colored flowing linen pants, or pull-on jeans (more comfortable); simple flats or sandals; and hippie-ish flowing tops or interesting (to me) more fitted tops, in cotton, linen, or silk. I love color in my tops - and notice that I can wear completely different colors than I could before my hair got white.

Lately, I’ve started to wear “monos” in Spain (jumpsuits) and long dresses, which are very popular there - mostly in light colors and patterns.

Also, I love to knit, and have about 30 sweaters in all shapes, weights, styles, and colors that I truly love to wear.

Wish I could include a couple of pictures in my comment to show you what I mean!

Thanks for starting this conversation - fascinating to read others’ comments, too -

Sari Botton's avatar

I love that you've never thought about "dressing your age" Erika! How liberating. Sounds like a nice style.

Erika Andersen's avatar

Thank you - it is liberating. I think part of it is that my mom never thought about it, either. When i was a kid in the fifties and sixties, she wore cut-offs and tennis shoes, when all her contemporaries were in shirtwaists and ballet flats. I liked it. :-)

Susan's avatar

So here with ya. And one word: ROUCHA!! "Clothing that conveys intellect, strength, and ease," they're not lying! Funky yet elegant, kinda pricy (well, similar to full-price Eileen Fisher), but get on their list for sales, they're great. Comes with a note telling you how to wear the clothes, I mean, I suck at dressing and this has changed my life.

Kristi Coulter's avatar

And another “r” brand, Ruti. Their skirts and pants are among the best I own, interesting and a little architectural without screaming “look at me, aren’t I just so QUIRKY?” about their wearer. I’m a huge fan.

Sari Botton's avatar

I’ll check them out! (I think maybe someone else mentioned Ruti in this thread, too.) PS Good luck in your new home, Kristi. 💕

Kristi Coulter's avatar

Thank you! We LOVE it here so far! (And will still be fleeing to LA during the winter, lol.)

Sari Botton's avatar

Oh, nice! I kind of love LA, although I’ve never spent more than a week at a time there, so I have no idea what it’s like to be an actual resident.

Susan's avatar

oh and I'm 61 and artsy-ish, like to look casual but neat.

Sari Botton's avatar

I identify as “artsy-ish” too.

Sari Botton's avatar

I’ll check them out…

Tiffany Lee Brown—BurningTarot's avatar

Alas, no petite sizes at Rocha from what I can see. Fellow 5' 0" person here.

Elise Seyfried's avatar

I actually just wrote about this in a humor piece for Next Avenue...https://www.nextavenue.org/dressing-my-ages/

Elena Brunn's avatar

What a wonderful essay!

Elise Seyfried's avatar

That’s so nice of you! Thank you!

Sari Botton's avatar

Oh, nice. I'll check it out!

Elise Seyfried's avatar

thanks so much!

Kimberly Diaz's avatar

I just checked out your essay and it resonated so much. Fun piece!

Elise Seyfried's avatar

Awww thanks very much!!

Lynda Rushing's avatar

I'm 68 and have been wearing Eileen Fisher for decades and my own beautiful 37 y.o. daughter loves them too. I'm also short (5'2") and try to get her clothes in petites. It's true that some of the styles can look shapeless, particularly if you are on the shorter side and her sizing can be off so you need to try on multiple sizes for different outfits, but her clothes are timeless and last forever. Plus are great for travel! And I love her commitment to sustainability. Also, she has great sales on-line but you have to move fast. She has a lot of followers and the best stuff gets scooped up fast! BTW, you look great in all of the pics, Sari. Sixty will be a (fashionable) breeze!

Kathryn Porterfield's avatar

Dacy Gillespie could help you! Check out Mindful Closet on Substack.

Sari Botton's avatar

Will do! I think I already follow her…

Liz Gumbinner's avatar

Not to be another person who says “you look great in that!” But you do. When you feel good about yourself, that’s what comes through. And you have those rad shoes and stockings and to me, that’s what makes the outfit look cool. A well-made black dress is a well-made black dress, whatever label is in there. Your style shines through!

PS I have also called myself Eileen Fisher years old. And yet! I started wearing some Eileen Fisher pieces in my 30s but I wouldn’t tell people because they thought they were “mom clothes.” For me it came down to the accessories. New earrings or Fluevog boots does the trick.

I still have the more timeless pieces; they are well-crafted and flattering, and as with any label, it’s how you wear them. ✨ Do you, Sari!